I'm not super knowledgeable Edward, but I can confirm you want at least a 330HP diesel, especially if you're planning on towing an enclosed trailer. Otherwise it has to work to hard and the exhaust gas temps climb to high, causing you to have to let up on the throttle, which makes you slow down, etc.

An enclosed trailer is great, but you will end up putting a lot of stuff in it (hence the need for the bigger diesel). We have a triple axle and Rob loves it.